Carbon Nucleophiles in the Mitsunobu Reaction. Mono- and Dialkylation of Bis(2,2,2-trifluoroethyl) Malonates

James M Takacs, Zhenrong Xu, Xun Tian Jiang, Alexei P. Leonov, Gregory C. Theriot

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

(Matrix Presented) Simple dialkyl malonate esters, for example diethyl malonate, exhibit relatively limited scope as carbon nucleophiles in the Mitsunobu dehydrative alkylation reaction. In contrast, bis(2,2,2-trifluoroethyl) malonate readily undergoes dehydrative alkylation with primary alcohols, and using only a slight excess of malonate gives monoalkylated product in good yield. Some secondary alcohols can also be employed, and bis(2,2,2-trifluoroethyl) malonates can be used in a second dehydrative alkylation to give dialkylated products in good to excellent yield.

Original languageEnglish (US)
Pages (from-to)3843-3845
Number of pages3
JournalOrganic Letters
Volume4
Issue number22
DOIs
StatePublished - Oct 31 2002

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Malonates
Nucleophiles
nucleophiles
alkylation
Alkylation
Carbon
carbon
alcohols
Alcohols
products
esters
Esters
matrices
malonic acid

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Carbon Nucleophiles in the Mitsunobu Reaction. Mono- and Dialkylation of Bis(2,2,2-trifluoroethyl) Malonates. / Takacs, James M; Xu, Zhenrong; Jiang, Xun Tian; Leonov, Alexei P.; Theriot, Gregory C.

In: Organic Letters, Vol. 4, No. 22, 31.10.2002, p. 3843-3845.

Research output: Contribution to journalArticle

Takacs, James M ; Xu, Zhenrong ; Jiang, Xun Tian ; Leonov, Alexei P. ; Theriot, Gregory C. / Carbon Nucleophiles in the Mitsunobu Reaction. Mono- and Dialkylation of Bis(2,2,2-trifluoroethyl) Malonates. In: Organic Letters. 2002 ; Vol. 4, No. 22. pp. 3843-3845.
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